— 130 — 



volume of ether. Shortly after the addition of the calculated quantity of 

 bromine (a possible excess of bromine may be removed by adding a few 

 drops of the hydrocarbon) the tetrabromide separates out in the form of a 

 solid cristalline paste. 



By inverting linaloolene and dihydromyrcene Semmler obtained cyclo- 

 linaloolene and q/cZodihydromyrcene. Linaloolene being identical with 

 dihydromyrcene, the same applies to the products of inversion. In the 

 case of dihydromyrcene Semmler carried out the inversion-process by 

 means of a mixture of glacial acetic and sulphuric acids. With regard 

 to this process he remarks 1 ): "this inversion is most easliy carried out 

 with glacial acetic acid and sulphuric acid, where, theoretically, an alcohol 

 should be expected". 



Working at a low temperature it is not particularly difficult to isolate 

 the alcohol in question. From 200 g. dihydromyrcene we obtained from 

 120 to 130 g. c^/cZodihydromyrcene and between 64 and 67 g. ester; the 

 latter boiling between 97 and 103° (12 mm.). The constants of the two 

 ester-fractions were as follow: 



I. di 5o 0,8780, n D15 o 1 ,44741 , ester v. 271 , mol. refr. found 60,61 ) caic. as 

 II. d 15o 0,8857, n D150 1,44549, ester v. 279, mol. refr. found 58,8 J c 12 h 22 o 2 /t 59,67. 



The alcohol obtained by saponification gave: 



I. Fract. 

 II. Fract. 



III. Fract. 



IV. Fract. 



calc. as 

 Cio H^ O ft 



49,438. 



B. p. 92 to 92,5° di5° 0,8563, n D i 5 o 1,45591, mol. refr. found 49,54, 

 (12 to 13 mm.) or di 5 o 0,8557, n D i5o 1 ,45471 , „ „ 49,48, 



200° at atmosph. dl50 ,8564, n D15 o 1 ,45641 , „ „ 49,50, 



pressure. ^ q^jq^ nwo j ^553^ ^ ? 49^ 



0,1456 g. subst: 0,4099 g. C0 2 , 0,1556 g. H 2 0. 

 Found Calc. as Ci H 20 O 



C 76,81% 76,92 °/o 



H 13,06°/o 12,82°/o 



When gently heated with formic acid the alcohol gave off water; 

 towards oxidation with chromic acid in glacial acetic acid and bichromate 

 in dilute sulphuric acid it was very stable, and the reaction did not give 

 rise to any ketone or aldehyde. With phenylisocyanate it yielded a phenyl- 

 urethane (m. p. 61°) which crystallised out in fine needles. 



Oxidation with a 1 / 2 °/o solution of permanganate of potassium yielded 

 as the principal product of reaction a glycerol, b. p. 165 to 170° (7 mm.), 

 together with a lactone and succinic acid. 



0,1299 g. subst.: 0,2995 g. C0 2 , 0,1269 g. H 2 0. 

 Found Calc. as Ci H 22 O 3 

 C 62,87°/o 63,13% 

 H 11,94% 11,57% 



J ) Bed. Berichte 34 (1901), 3128. 



